OXIDATIVE HAIR DYEING 133 I#TER•EDIATE DYES IN THe- HAll/ •!•enta Hydroxyindoani line v I ( l ) i•-Dlamine (li) Ox, O•'een I TriDn•: lear\• nuclear, I amine B•'own I Polyme•'lc I Indoani line Oxe FADII•G •lagent, a Aminoindoani line '• Blue Indamine • I (i) p-Diaminox. (li) Bluish B•own Trlnuelea• T•inuelear Dye Dye Higher polymer •' Red Diamin•o•_ Higher polymer and/or phenazine and/or Hydro lyric C leav- and/or Hydro lytic C leav- age Products Magenta Amino- age Products (brown) indoaniline (brown) Figure 16. Role of meta difunctional benzenes in oxidative hair dyeing (14) Corbett, J. F., Intermediates and products in oxidative hair dyeing, Proc. Joint Conf. Cosmet. Sci., Washington, D.C., 159 (1968). (15) Corbett, J. F., Benzoquinone imines, Part II, J. Chem. Soc., B., 1969, 213. (16) Corbett, J. F., Benzoquinone imines, Part VIII, Ibid., 1970, 1502. (17) Corbett, J. F., Benzoquinone imines, Part VI, Ibid., 1969, 827. (18) Shah, M. J., Tolgyesi, W., and Britt, A.D., Cooxidation of p-phenylenediamine and resorcinol in hair dyes, J. Soc. Co met. Chem., 23, 853 (1972). (19) Shah, M. J., Chromatographic and spectroscopic studies of the oxidation products of p-phenylenediamine and resorcinol, Ph.D. thesis, George Washington University, 1970.

134 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS (20) (21) (22) (2s) (24) (25) (26) (27) (28) (29) (30) (31) (36) (37) Rayette, Can. Patent 607,489 (1960). Schwarzkopf, Get. Patent 1,144,879 (1963). Schwarzkopf, U.S. Patent 3,210,252 (1965). Wella, Belg. Patent 649,310 (1963). Wella, Brit. Patent 868,325 (1959). L'Oreal, U.S. Patent 3,591,323 (1966). L'Oreal, Brit. Patent 1,025,916 (1960). L'Oreal, Brit. Patent 1,079,553 (1961). L'Oreal, Brit. Patent 1,228,552 (1971). L'Oreal, Brit. Patent 1,229,517 (1971). L'Oreal, Brit. Patent 1,234,598 (1971). Husmeyer, H. H., Haar-farbung und Haartonung, Riechst., Aromen, Koerperpfiegem., 1971, 181. (32) Corbett, J. F., The Chemisttit of Synthetic Dyes, Vol. V, ed. K. Venkataraman, Aca- demic Press, New York, 1971, p. 475. (33) L'Oreal, U.S. Patent 3,591,323 (1971). (34) Cox, H. E., The chemical examination of furs in relation to dermatitis, Analyst, 59, 3 (1934). (35) Cox, H. E., Hair dyes. II. The functions and reactions of phenols, Ibid., 65, 393 (1940). Sidi, E., and Zviak, C., Problems Capilliaires, Dunod, Paris, 1966, p. 140. Nietzki, R., and Maeckler, H., Ueber Resorcin und Orcinfarbstoffe, Chem. Bet., 23, 723 (1890). (38) Musso, H., and Wager, P., Neue Synthesen fur 7-Aminophenoxazone-(2), Ibid., 94, 2551 (1961). (39) Brody, IV., and Burns, M. S., Studies concerning the reaction of oxidation dye inter- mediates, ]. Soc. Cosmet. Chem., 19, 361, (1968). (40) Corbett, J. F., Benzoquinone imines, Part III, ]. Soc. Dyers Colour., 85, 71 (1969). (41) Bernthsen, A., and Schweitzer, H., Das Phenazin als Muttersubstanz der Farbstoffe der Toluylenerothgruppe, Annalen, 236, 343 (1886). (42) Tolgyesi, W., personal communication, 1970. (43) Corbett, J. F., Benzoquinone imines, Part X, J. Chem. Soc. (Perkin 2), 1972, 999. (44) Musso, H., and Matthies, H. G., Uber Orceinfarbstoffe, V, Chem. Bet., 90, 1814 (1957). (45) Musso, H., Matthies, H. G., Kramer, H., and Hocks, P., Uber Orceinfarbstoffe, XI, Ibid., 93, 1782 (1960). (46) Corbett, J. F., Benzoquinone imines, Part I, 1. Chem. Soc., B., 1969, 207. (47) Corbett, J. IV., Benzoquinone imines, Part VII, Ibid., 1970, 1418. (48) Sibert, G., Ursatin, Ullmann's Encyklopadie der technischen Chemie, Urban and Schwarzenberg, Berlin, 1962, Vol. 13, p. 110. (49) Ginzel, A., Die Chemic der Pelzfarbstoffe, Melliand Textilber., 29, 384 (1948).